(2S,3R,4S,5S,6R)-2-[(3S)-5-[(1S,2S,4aS,5R,8aR)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 454f1e9c-cffa-45b0-920f-a08a966a3fd7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(3S)-5-[(1S,2S,4aS,5R,8aR)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(CCCC2(C1CCC(C2CCC(C)(C=C)OC3C(C(C(C(O3)CO)O)O)O)(C)O)C)CO
• SMILES (Isomeric): C[C@]1(CCC[C@@]2([C@@H]1CC[C@]([C@H]2CC[C@@](C)(C=C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)(C)O)C)CO
• InChI: InChI=1S/C26H46O8/c1-6-24(3,34-22-21(31)20(30)19(29)16(14-27)33-22)12-8-18-25(4)11-7-10-23(2,15-28)17(25)9-13-26(18,5)32/h6,16-22,27-32H,1,7-15H2,2-5H3/t16-,17-,18+,19-,20+,21-,22+,23+,24-,25-,26+/m1/s1
• InChI Key: VHDWDVBOCYKGBG-OAFULXSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₆O₈
• Molecular Weight: 486.60 g/mol
• Exact Mass: 486.31926842 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.7955	79.55%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5955	59.55%
OATP2B1 inhibitior	-	0.5735	57.35%
OATP1B1 inhibitior	+	0.8307	83.07%
OATP1B3 inhibitior	+	0.8747	87.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7828	78.28%
P-glycoprotein inhibitior	-	0.5923	59.23%
P-glycoprotein substrate	-	0.7793	77.93%
CYP3A4 substrate	+	0.6770	67.70%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.7982	79.82%
CYP2C9 inhibition	-	0.8993	89.93%
CYP2C19 inhibition	-	0.8167	81.67%
CYP2D6 inhibition	-	0.9556	95.56%
CYP1A2 inhibition	-	0.8624	86.24%
CYP2C8 inhibition	+	0.6037	60.37%
CYP inhibitory promiscuity	-	0.9646	96.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7392	73.92%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9449	94.49%
Skin irritation	-	0.6535	65.35%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8258	82.58%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7047	70.47%
skin sensitisation	-	0.9143	91.43%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7687	76.87%
Acute Oral Toxicity (c)	III	0.4628	46.28%
Estrogen receptor binding	+	0.6659	66.59%
Androgen receptor binding	+	0.6041	60.41%
Thyroid receptor binding	+	0.5357	53.57%
Glucocorticoid receptor binding	+	0.6464	64.64%
Aromatase binding	+	0.6950	69.50%
PPAR gamma	+	0.5788	57.88%
Honey bee toxicity	-	0.7210	72.10%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9250	92.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.30%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.55%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.23%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.08%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.45%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.40%	95.89%
CHEMBL206	P03372	Estrogen receptor alpha	91.00%	97.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.17%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.00%	96.21%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	89.51%	97.47%
CHEMBL1937	Q92769	Histone deacetylase 2	89.39%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	89.31%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.17%	95.50%
CHEMBL2581	P07339	Cathepsin D	88.36%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	88.30%	98.10%
CHEMBL325	Q13547	Histone deacetylase 1	88.23%	95.92%
CHEMBL233	P35372	Mu opioid receptor	88.22%	97.93%
CHEMBL259	P32245	Melanocortin receptor 4	87.42%	95.38%
CHEMBL3524	P56524	Histone deacetylase 4	87.22%	92.97%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.79%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.61%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.59%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.56%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.41%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.80%	97.14%
CHEMBL1977	P11473	Vitamin D receptor	83.56%	99.43%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.88%	91.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.91%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	80.77%	92.50%
CHEMBL2996	Q05655	Protein kinase C delta	80.21%	97.79%

Plants that contains it

• Sticherus quadripartitus

Cross-Links

• PubChem: 162923426
• LOTUS: LTS0032971
• wikiData: Q105286330